


Breaking and Entering

by Anonymous



Category: Original Work
Genre: 1930s, Crossdressing, Crying, F/M, Gags, Humiliation, Non-Consensual Oral Sex, Rape/Non-con Elements, Rough Oral Sex, Vaginal Sex
Language: English
Status: Completed
Published: 2019-11-18
Updated: 2019-11-18
Packaged: 2021-02-08 12:35:13
Rating: Explicit
Warnings: Rape/Non-Con, Underage
Chapters: 1
Words: 2,518
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21476098
Author URL: https://archiveofourown.org/
Summary: God, she looked good like that, bent over the bed and wriggling, all tied up in red and green like a Christmas present. He'd been meaning to tie her to a chair, finish the job, and leave her to be discovered along with the empty pockets and purses. But now he was thinking there was another pocket he'd like to pick.
Relationships: Original Female Character/Original Male Character
Comments: 6
Kudos: 80
Collections: Anonymous, Consent Issues Exchange 2019





	Breaking and Entering

**Author's Note:**

  * For [allyoops](https://archiveofourown.org/users/allyoops/gifts).

The Roaring Twenties had given way to the leaner Thirties, but you wouldn't know it by the lavish Christmas party at the Mortimers' house. From trimming the tree to cooking the feast to serving the guests, there was far more to do than the Mortimers' regular staff could handle, so they borrowed additional help from their friends. Genial Mr. Harrison, a relative newcomer to their circle, had been happy to lend them his own recently hired housekeeper, a tall young woman called Kate. She was homely and shy, with a low voice and a thick Irish accent that fell heavily on their refined American ears, but Harrison assured the Mortimers she would make herself useful, and really, all they needed was another pair of hands.

James O'Leary wove through the crowded living room, handing out cocktails and Champagne that still carried the thrill of the forbidden, though Prohibition was dead and buried. In his starched black dress and white apron, topped with a brown wig and a white cap, he looked like just another maid. He had thought it was a pretty kooky scheme when Harrison first explained it, but as guest after guest took glass after glass without ever so much as glancing at him, he realized how perfectly this getup let him move around the house without being noticed. Tomorrow no one would remember his face.

The biggest risk was that one of the other servants might give him a close look. Fortunately, they were all Negroes and chummy with one another already, and they wouldn't question Mr. Harrison's Irish girl keeping to herself. O'Leary liked Negroes fine, as it happened, but "Kate" was standoffish, and by the time the partiers sat down to dinner, he wouldn't have been welcome in the kitchen gossip session even if he'd wanted to join it.

"Fix yourself a plate," said Nell, the Mortimers' housekeeper, "and then you can go park yourself in the upstairs bedroom where the coats are, in case anyone wants to leave early."

O'Leary nodded meekly, hiding his delight. Nell clearly thought she was exiling him, but that bedroom full of furs and purses was exactly where he wanted to be.

He wouldn't have minded some of the beef roast that the Mortimers and their guests were about to enjoy, but he planned to be long gone by the time the scraps made it back into the kitchen. He contented himself with potatoes and carrots roasted in the beef drippings and a thick slice of buttered bread. "Mind you wash your hands good and well," Nell cautioned him. "You don't want your greasy fingers on Mrs. Lewis's mink."

With squeaky-clean hands, O'Leary went up to the guest bedroom, where a four-poster bed was heaped high with coats and bags, and began rifling through them.

He'd pocketed two pairs of earrings, a gold watch, and a decent amount of cash when he heard footsteps on the stairs. He straightened up, surprised. No one ever actually left a party like this early. It was probably another servant, or a member of the family. He quickly sat in a chair by the bed, picked up a book, and tried to look like he'd been reading it this whole time.

The door opened and Deedee Mortimer came in. She glanced at him just long enough to register his presence and then ignored him, going over to the secretary desk in the corner and rummaging about in the cabinet. Since her back was to him, he allowed himself to take a good long look at her. She was a fresh young thing, perhaps sixteen, and her backless emerald green satin dress clung to her figure and highlighted her creamy skin and auburn hair. She sported a gold necklace hung with a beautiful pear-shaped emerald and diamond pendant that O'Leary figured cost at least $500. When she folded up the desk and bent over to look in one of the lower drawers, he saw that a column of tiny buttons descended from the waist of the gown, highlighting the curve of her ass. Speaking of drawers, he wondered whether she was wearing any. There sure didn't seem to be room for them under the snug, shimmering fabric.

His dick stirred inside his own feminine undergarments. Harrison had insisted that the padded brassiere was needed to fill out the dress, and the girdle gave O'Leary something like a womanly shape and held up his stockings. It had been reasonably comfortable right up until Miss Mortimer flaunted her curves at him; now it was a little confining.

Finally she found whatever she'd been looking for—a small book or notebook of some kind—and shut the drawer. O'Leary hastily looked back at his own book as she strode past him, her gardenia perfume wafting behind her, and left the room without giving him a second glance, closing the door behind her.

He sighed with relief and set the book aside. He needed to be long gone from here by the time people came for their things; he didn't want to rush, but it was best to be swift.

He had just stuck his hand into someone's gold lamé evening bag when the door opened again and Miss Mortimer came back in.

She stared at him; he stared at her. "You thief!" she gasped. "How dare you—"

O'Leary dropped the bag and lunged for her, pinning her up against the wall with his body pressed against hers and his hand over her mouth. Her eyes were wide, more angry than frightened. "Not a word, miss," he hissed. "Not a bloody word more."

She mumbled something. He tighted his hand, digging his fingers and thumb into her cheeks a little, and she quieted. "That's right," he said, "be a good girl."

At this Miss Mortimer looked outraged and made more noises against his hand. O'Leary sighed. _One of those,_ he thought. _Those are always trouble._

He made a long arm and nabbed a red wool scarf from the bed. In a moment he had it wrapped twice around her mouth and tied behind her head. She pulled ineffectually at his arms, but he was a good foot taller and considerably stronger, so he just ignored her until he was done. Then he grabbed her hands, shoved her over to the bed, and used another scarf, this one dark red silk, to tie her wrists behind her back.

God, she looked good like that, bent over the bed and wriggling, all tied up in red and green like a Christmas present. He'd been meaning to tie her to a chair, finish the job, and leave her to be discovered along with the empty pockets and purses. But now he was thinking there was another pocket he'd like to pick. He'd have to be quick about it, but she was too tempting to pass up. 

He shoved her gown up, tearing the thin, tight fabric, to reveal a stretchy girdle and delicate seamed stockings. "No bloomers, eh?" He chuckled. "You're a naughty one."

She started shrieking and he was glad he'd gotten that scarf around her mouth. Even with that, he was a bit concerned someone might hear. "Shut up," he said conversationally, slapping her ass. She kept yelping, so he hit her again and again until she was reduced to quiet sobs.

O'Leary couldn't see an easy way to get the clinging elastic girdle off her, so he pulled out his pocket knife and sliced it up the center, baring her ass and her back. Two more swipes of the knife took care of the rear garters and let him open the girdle all the way. His unwrapped present squirmed as he ran a hand over her soft skin. 

Her ass was beautifully curved; it must have been straining under the confines of the elastic. The seamed stockings accentuated her long legs. Her skin was so pale. All he wanted to do was cover it with red marks. If he had the time to do this properly, he'd give her a paddling she'd never forget. A spoiled brat like her had probably never been spanked in her life.

The knife was still in his hand. He laid the cold flat of the blade against her right cheek just to see her jump. Now her muffled noises were fearful and pleading. He liked that much better than the sass.

"You want that scarf off your mouth?"

A frantic nod.

"Here's the deal, see. I'll take it off, because I like those little whimpers you're making and wouldn't mind hearing them better. But one smart word from you..." He ran the blunt edge of the knife over her skin, knowing she couldn't tell it wasn't sharp. "You're marked for good. And if you scream, your daddy will find you here with this knife in you and me gone out the window." None of this was true—he was no killer, and he sure as shit didn't fancy the long drop out the second-story window—but as long as she thought he was prepared to off her, he figured he'd be safe.

There was more frantic nodding. Cautiously, he untied the scarf and unwound it. She turned her head to the side and sucked in a deep breath, and then another. Her face was red and streaked with tears. She didn't talk back and she didn't scream. Good.

While she caught her breath, O'Leary unsnapped his own garters and shoved his girdle down and off, kicking it into the corner of the room. Miss Mortimer watched him over her shoulder, first in puzzlement and then in shock. "You're a man!" she gasped.

"Oh, you're about to find that out for certain sure." He hiked up his black skirt, tucking it into his apron to keep it out of the way, and showed her his cock, stroking it roughly and pulling back the foreskin so she could see the whole of it. Her eyes were wide. "You like what you see, girlie? Seen a few of these, I bet, a sweet dish like you."

She tossed her head, as best she could among the fur coats and the disarray of her dress. "So what if I have," she said, not more than halfway convincingly.

He grinned. "Then I bet you know what to do with that smart mouth of yours." Not waiting for an answer, he pulled her hips back off the bed. She stumbled in her pumps and he shoved her down to her knees. He fisted one hand in her disheveled hair and showed her the knife with the other. "If I feel teeth, you feel this."

She opened her mouth to reply and he pushed his cock in, getting right back into her throat on the first thrust. She struggled, but he had a good grip on her hair. "Suck it," he ordered, starting to fuck her mouth slowly and deeply. 

She tried, but it was clear she had no idea what she was doing, and in any case he didn't care. Her throat gripped him every time he pushed in, and when he pulled back she inhaled desperately and made panicky noises that turned him on even more. Her face was a picture, all flushed and sweaty with tears at the corners of her eyes. 

He growled and started moving faster, using her hair to jerk her mouth up and down on his cock. Little cries came from her mouth as her hands twisted futilely behind her. She was so slick and wet and warm, her tongue moving erratically, her throat working as she gagged on him. Heavenly.

Finally he had to stop or risk spending himself in her mouth. He pulled the girl away and admired her face for a moment as she gasped and coughed. Then he hauled her back to her feet and bent her over the bed again.

O'Leary put the knife away—she knew better than to make noise now—and stuck a finger up into her cunt. She gasped and pulled away. "Ooh, you're wet," he sneered, though she wasn't very. That was fine, she'd gotten him wet enough with her mouth.

Gripping her hips, he pushed in, relishing her virginal tightness. She cried out, so he dragged someone's mink coat over her head to mask her noises. 

He had to work his way in with short hard thrusts, ramming her open, but finally he was buried all the way inside her. She was crying again, her cunt squeezing with every sob as it frantically tried to expel him. It was so sexy that he had to stop and take deep breaths to control himself. At last the urge to climax passed and he let himself start to fuck her properly, dragging his cock out and then shoving it all the way back in.

She was dry at first, and the friction was almost too intense, but soon she started to get wetter. "You love it, don't you," O'Leary said, digging his fingers into her hips hard enough to bruise and thrusting like he was mining for gold inside her. "Everyone who sees you will know now. It shows on a woman, when she loves getting fucked. Men will smell it on you."

Miss Mortimer cried harder, her body heaving. 

"Those are some good... crocodile tears," he panted. He couldn't hold back much longer. "But you know... you want this... you love my cock... yeah, you love it—"

Orgasm overtook him and he bit his lip to keep from yelling. He pushed in as deeply as he could and felt her pussy almost suck his load out of him. "Good girl," he said softly.

When he pulled Miss Mortimer to her feet, she looked completely ravished. Her hair was a tangled mess; her gaze was vacant. She didn't fight as he put her in the chair by the bed, tied her wrists to it, and wrapped the wool scarf around her mouth again. The jolly red wool was incongruous against her flushed, tearstained face. 

Grabbing her chin and forcing her to look at him, he used the trailing shreds of her gown to wipe off his cock and then untucked his skirt. Without his girdle, his stockings would eventually fall down, but putting it back on would take too long. He'd wasted enough time on this little side job—well, not wasted, he amended. It was time well spent. But now he had to hurry.

He went through the last of the coats and bags with professional efficiency. Satisfied that he'd taken everything of value, he turned to Miss Mortimer, who seemed to be slowly coming out of her daze, and realized he'd forgotten one thing. Delicately, he removed her necklace and pocketed it with the rest.

"Thanks, doll," he said, patting her cheek. "You were great. Let's do this again sometime."

She turned her head away, blinking as fresh tears spilled down her face.

O'Leary adjusted his wig and cap in the vanity mirror, did his best to smooth the wrinkles in his dress, and left without a backwards glance.


End file.
